Deal Desk Manager

About the Role

Sentry's Revenue Operations team is built around three pillars — Analytics, GTM Technology, and Deal Desk — and we're hiring a Deal Desk Analyst to strengthen the Deal Desk. This role is for someone who is curious about why deals are structured the way they are, spots inefficiencies early, and sees our CPQ and Salesforce environment as a system to be improved. You'll partner closely with our Senior Deal Desk Manager to keep sales moving without bottlenecks. Your mandate is twofold: handle deals with speed and consistency, and help automate and simplify the deal desk experience so routine work becomes self-service for reps. This role offers growth into a deep operator and systems thinker for those who thrive on bringing order to chaos and eliminating unnecessary manual steps.

Responsibilities

• Own end-to-end processing of deals — including quote creation, discount review, order form generation, and approval routing — with minimal escalation and fast turnaround.
• Partner with our Senior Deal Desk Manager to ensure coverage across the full deal portfolio so no single point of failure exists on the team.
• Become an expert in our CPQ system and Salesforce integration, advocating for improvements and working alongside our GTM Tech team to drive changes.
• Document pain points, propose solutions, and help design and implement self-service guardrails and automation to reduce manual Deal Desk intervention.
• Build and maintain deal desk playbooks, approval matrices, and process documentation to create consistency and reduce re-review.
• Support pricing updates by ensuring changes are accurately and promptly reflected in CPQ, and flag downstream impacts before they become problems.
• Identify patterns across deal data — approval rates, exception types, deal velocity — and surface insights that inform policy and pricing decisions.

You'll Love This Job If You

• Get frustrated by manual work that could be automated and take action to fix it.
• Can hold your own in conversations with sales reps pushing for discounts and with systems engineers discussing workflow configurations.
• Like operating with autonomy while staying tightly coordinated with a small team.
• Enjoy making things simple through thoughtful, hard work.
• Believe a good deal desk shouldn’t be a bottleneck; it should make deals go faster.
• Are energized by a company actively re-imagining processes as GTM technology evolves, and want to shape what comes next.

Qualifications

• 5+ years of experience in Deal Desk, Sales Operations, Revenue Operations, or a closely related function at a B2B SaaS company.
• Hands-on experience with CPQ tools (Dealhub, Salesforce CPQ, MonetizeNow, or similar) and a clear understanding of quoting logic, product catalogs, and approval workflows.
• Comfortable in Salesforce; familiar with objects, fields, reports, and able to collaborate with Salesforce admins on needed changes.
• Experience handling the full deal lifecycle: quoting, redlines, order forms, and booking.
• Strong analytical instincts; able to build models or reports to answer key questions and identify which questions are worth asking.
• A demonstrated habit of improving inherited processes, not just executing them.
• Experience using AI tooling (Copilot, ChatGPT, or purpose-built RevOps tools) to accelerate deal review, summarization, or exception routing.

Nice to Have

• Familiarity with SaaS pricing models including usage-based, ramped, or multi-product structures.
• Experience supporting both new business and renewal motions with an understanding of why clean separation of roles matters.